Water → HCID 20143022, compound

HRID 649313Notes

Reaction equation

HRID 649313 reaction equation
Cl[C:2]1([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1.[C-:21]#[N:22].[Na+].C(OCC)(=O)C.O>CS(C)=O>[C:21]([C:2]1([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:7](=[O:8])[N:6]([CH3:9])[C:5]2[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=2[S:3]1)#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 20143033HCID 20143033, compound

Product 1

HCID 20143022HCID 20143022, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2-chloro-3,4-dihydro-2-(4-hydroxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (10.0 g, compound No. 2) in dimethylsulfoxide (100 ml), sodium cyanide (8.0 g) is added. The mixture is stirred for 2 hours at room temperature, and poured into a mixture of ethyl acetate and water. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 6.9 g (71.0%) of the titled compound.

Workup

  1. washThe organic layer is washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdac9a3545cb4bde82e77a2bf32ff0e7
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

Loading…